Principal, AI Capability & Reskilling

Avalara•UNAVAILABLE, UNAVAILABLE

10d•Remote

About The Position

At Avalara, we are building a future where AI isn't just something we use—it's seamlessly embedded into how we work, driving faster decisions, fewer manual handoffs, and creating more time for high-impact work requiring human judgment. As the Enterprise AI Capability Program Lead, you will own the system that makes this shift possible. You'll lead our enterprise reskilling and AI capability program, guiding managers, leaders, and eventually all employees from AI awareness to structured experimentation and workflow redesign.

Requirements

Bachelor's degree in business, organization development, human resources, industrial-organizational psychology, or a related field, or equivalent experience.
Experience teaching, coaching, or facilitating for adult/professional audiences, comfortable being the person in the room, not just the person who designed the curriculum.
8+ years designing and delivering enterprise capability-building or reskilling programs at scale, with a track record tying program design to measured business outcomes, not completion rates alone.
Solid grounding in organizational design (operating models, role clarity, span of control, decision rights, systems thinking), with ability to build credible tools and coach leaders through the redesign process.
Deep, current fluency in generative and agentic AI, with the ability to translate capabilities into role, skills, and workforce implications, and hands-on experience applying AI tools to real work (prompt engineering, AI-augmented workflow design, AI-augmented analysis).
Strong judgment: able to connect org design, AI capability, and workflow optimization into one coherent, pragmatic program.
Comfort working with data and measurement, particularly in demonstrating the value created by capability building programs.

Nice To Haves

Experience building and mobilizing champion networks or communities of practice.
Experience running a comparable AI-fluency or reskilling program on an enterprise scale.
Process-improvement certification (e.g., Lean, Six Sigma, Kaizen) or Business Process Management certification (e.g., ABPMP CBPA).

Responsibilities

Design and own the multi-stage capability program that takes employees and managers from AI awareness to structured experimentation, to identifying real use cases in their own work, to changing how that work gets done, and evolving the program's design as the organization matures.
Personally teach, coach, and mentor managers and functional leaders as they build fluency and lead redesign in their own teams, including facilitating workshops and working sessions across functions globally.
Build reusable tools, templates, and frameworks, including ones that help leaders break roles into tasks, assess AI suitability, and redesign around the human-AI boundary so the work scales beyond direct engagement.
Translate complex AI and org-design concepts into approachable, compelling content for a management audience.
Build the infrastructure that turns individual experimentation into organizational learning: mechanisms for surfacing use cases, an AI champions network across functions, and forums where practical wins get shared and repeated.
Own measurement of the program's impact as evidenced by the change in work itself (e.g., speed, quality, capacity redirected to higher value tasks) versus adoption metrics.
Progressively expand the program beyond managers to a full employee-wide reskilling agenda, sequencing where the next capability gap or opportunity matters most.
Own the long-term, continuous improvement of both the capability program and manager effectiveness in this area; this is a durable mandate you keep improving, not a program you launch once and hand off.
Report regularly to senior leadership on program impact, with a clear, evidence-based answer to “how is the organization working smarter because of this program.”